EP0403618B2 - Aldimino- oder ketimino-oxy-ortho-tolylacrylsäure-methylester, ihre herstellung und diese enthaltende fungizide - Google Patents

Aldimino- oder ketimino-oxy-ortho-tolylacrylsäure-methylester, ihre herstellung und diese enthaltende fungizide Download PDF

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Publication number
EP0403618B2
EP0403618B2 EP89913190A EP89913190A EP0403618B2 EP 0403618 B2 EP0403618 B2 EP 0403618B2 EP 89913190 A EP89913190 A EP 89913190A EP 89913190 A EP89913190 A EP 89913190A EP 0403618 B2 EP0403618 B2 EP 0403618B2
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EP
European Patent Office
Prior art keywords
methyl
chlorophenyl
ethyl
tolyl
cyclopropyl
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Expired - Lifetime
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EP89913190A
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English (en)
French (fr)
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EP0403618B1 (de
EP0403618A1 (de
Inventor
Hans Peter Isenring
Stephan Trah
Bettina Weiss
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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    • A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
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    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/28—Halogen atoms

Definitions

  • the present invention relates to substituted 2-phenyl-3-methoxyacrylic acid methyl esters of the general formula in which R 1 and R 2 have the following meanings: R 1 R 2 3,5-di (trifluoromethyl) phenyl methyl 2-fluoro-5-methylphenyl methyl 2-benzofuranyl methyl 2-quinolinyl hydrogen 4-fluorophenyl methyl 4-nitrophenyl methyl 4-chlorophenyl methyl 4-chlorophenyl Ethyl ⁇ -Phenylvesthenyl methyl o-tolyl methyl p-anisyl methyl 4-biphenylyl methyl cyclopropyl cyclopropyl ⁇ - (2-furyl) -questionedhenyl methyl ⁇ - (3,4,5-trimethoxy-phenyl) -relihenyl methyl ⁇ , ⁇ , ⁇ , -trifluoro-m-tolyl methyl 3-Bromophenyl methyl 2-chlorophen
  • the compounds according to the invention have fungicidal properties and are suitable as fungicidal active substances, in particular for use in agriculture and horticulture.
  • the invention further relates to a process for the preparation of the compounds according to the invention, fungicidal compositions which contain such compounds as active ingredients, and the use of such compounds and compositions for controlling fungi in agriculture and horticulture.
  • This reaction is a nucleophilic substitution which can be carried out under the reaction conditions customary in this regard.
  • the leaving group U present in the benzyl alcohol derivative of the formula (III) is preferably to be understood as meaning chlorine, bromine, iodine, mesyloxy or tosyloxy.
  • the reaction is conveniently carried out in an inert organic diluent such as a cyclic ether, e.g. Tetrahydrofuran or dioxane, acetone, dimethylformamide or dimethyl sulfoxide, in the presence of a base such as sodium hydride, sodium or potassium carbonate, a tertiary amine, e.g.
  • a trialkylamine especially diazabicyclononane or diazabicycloundecane, or silver oxide, at temperatures between -20 ° C and 80 ° C, preferably in the temperature range from 0 ° C to 20 ° C.
  • reaction can be carried out with phase transfer catalysis in an organic solvent such as methylene chloride in the presence of an aqueous basic solution, e.g. Sodium hydroxide solution, and a phase transfer catalyst, such as tetrabutylammonium hydrogen sulfate, take place at room temperature.
  • organic solvent such as methylene chloride
  • a phase transfer catalyst such as tetrabutylammonium hydrogen sulfate
  • the compounds of the formula I 'thus prepared can be isolated and purified by methods known per se. Any isomer mixtures obtained, e.g. E / Z isomer mixtures into which pure isomers are separated, for example by chromatography or fractional crystallization.
  • the starting materials of formula (III) can also be prepared in a manner known per se, e.g. as described in European Patent Publication No. 203,606 (BASF) and in the literature cited therein.
  • the compounds according to the invention have a fungicidal action and can accordingly be used for combating fungi in agriculture, horticulture and in wood processing. They are particularly suitable for inhibiting the growth or for destroying phytopathogenic fungi on parts of plants, e.g. Leaves, stems, roots, tubers, fruits or flowers, and on seeds and on harmful fungi that occur in the soil. Furthermore, wood-degrading and wood-staining fungi can be combated with the compounds according to the invention.
  • the compounds according to the invention are, for example, active in combating fungi of the classes Deuteromycetes, Ascomycetes, Basidiomycetes and Phycomycetes.
  • the compounds furthermore act, for example, against fungi of the genera Tilletia, Ustilago, Rhizotonia, Verticillium, Fusarium, Pythium, Gaeumannomyces, Sclerotinia, Monilia, Botrytis, Peronospora, Bremia, Gloeosporium, Cercosporidium, Penicillium, Ceratocystis, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorium, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rhynophephosphorus, Rh
  • the compounds according to the invention are distinguished by a prophylactic and curative action.
  • the compounds according to the invention act against phytopathogenic fungi under greenhouse conditions even at concentrations of 0.5 mg to 500 mg of active ingredient per liter of spray mixture.
  • doses of 20 g to 1 kg of active ingredient of the formula I 'per hectare and treatment are advantageously used.
  • the following are essentially suitable as solid carriers: natural minerals, such as kaolin, clays, kieselguhr, talc, bentonite, chalk, e.g. Sludge chalk, magnesium carbonate, limestone, quartz, dolomite, attapulgite, montmorillonite and diatomaceous earth; synthetic minerals such as finely divided silica, aluminum oxide and silicates: organic substances such as cellulose, starch, urea and synthetic resins; and fertilizers such as phosphates and nitrates, such carriers e.g. can be present as granules or powder.
  • natural minerals such as kaolin, clays, kieselguhr, talc, bentonite, chalk, e.g. Sludge chalk, magnesium carbonate, limestone, quartz, dolomite, attapulgite, montmorillonite and diatomaceous earth
  • synthetic minerals such as finely divided silica, aluminum oxide and silicates: organic substances such as cellulose, starch, urea
  • solvents or dispersing agents aromatics, such as toluene, xylenes, benzene and alkylnaphthalenes; chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes and methylene chloride; aliphatic hydrocarbons, such as cyclohexane and paraffins, for example petroleum fractions; Alcohols, such as butanol and glycol, and their ethers and esters; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; and strongly polar solvents or dispersing agents, such as dimethylformamide, N-methylpyrrolidone and dimetyhyl sulfoxide, such solvents or dispersing agents preferably having flash points of at least 30 ° C.
  • aromatics such as toluene, xylenes, benzene and alkylnaphthalen
  • liquefied gaseous extenders or carriers which are products which are at room temperature, are also suitable among the solvents or dispersants and are gaseous under normal pressure.
  • examples of such products are, in particular, aerosol propellants, such as halogenated hydrocarbons, for example dichlorodifluoromethane.
  • aerosol propellants such as halogenated hydrocarbons, for example dichlorodifluoromethane.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • the surfactants can be nonionic compounds, such as condensation products of fatty acids, fatty alcohols or fat-substituted phenols with ethylene oxide, fatty acid esters and ethers of sugars or polyhydric alcohols; the products obtained from sugars or polyhydric alcohols by condensation with ethylene oxide; Block polymers of ethylene oxide and propylene oxide; or alkyldimethylamine oxides.
  • the surfactants can also be anionic compounds, such as soaps; Fatty sulfate esters, e.g. Dodecyl sodium sulfate, octadecyl sodium sulfate and cetyl sodium sulfate; Alkyl sulfonates, aryl sulfonates and fatty aromatic sulfonates such as alkyl benzene sulfonates, e.g. Calcium dodecylbenzenesulfonate; and butylnaphthalenesulfonates; and more complex fatty sulfonates, e.g. the amide condensation products of oleic acid and N-methyl taurine and the sodium sulfonate of dioctyl succinate.
  • Fatty sulfate esters e.g. Dodecyl sodium sulfate, octadecyl sodium sulfate and cetyl sodium sulf
  • the surfactants can be cationic compounds, such as alkyldimethylbenzylammonium chlorides, dialkyldimethylammonium chlorides, alkyltrimethylammonium chlorides and ethoxylated quaternary ammonium chlorides.
  • lignin sodium and ammonium salts of lignin sulfonic acid, sodium salts of maleic anhydride-diisobutylene copolymers, sodium and ammonium salts of sulfonated polycondensation products made from naphthalene and formaldehyde and sulfite waste liquors.
  • dispersants which are particularly suitable as thickening or anti-settling agents, e.g. Methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol, alginates, caseinates and blood albumin can be used.
  • Suitable stabilizers are acid-binding agents, e.g. Epichlorohydrin, phenylglycidyl ether and soya epoxides, antioxidants, e.g. Gallic acid esters and butylated hydroxytoluene; UV absorbers, e.g. substituted benzophenones, diphenylacrylonitrile acid esters and cinnamic acid esters; and deskativators, e.g. Salts of ethylenediaminetetraacetic acid and polyglycols.
  • acid-binding agents e.g. Epichlorohydrin, phenylglycidyl ether and soya epoxides
  • antioxidants e.g. Gallic acid esters and butylated hydroxytoluene
  • UV absorbers e.g. substituted benzophenones, diphenylacrylonitrile acid esters and cinnamic acid esters
  • deskativators e
  • the fungicidal compositions according to the invention can also contain other active compounds, e.g. other fungicides, insecticides and acaricides, bactericides, plant growth regulators and fertilizers.
  • active compounds e.g. other fungicides, insecticides and acaricides, bactericides, plant growth regulators and fertilizers.
  • Such combination agents are suitable for spreading the spectrum of activity or for specifically influencing plant growth.
  • the fungicidal compositions according to the invention contain between 0.0001 and 85 percent by weight of compounds according to the invention as active ingredient (s). They can be in a form suitable for storage and transportation. In such forms, for example emulsifiable concentrates, the active ingredient concentration is normally in the higher range of the above concentration interval. These forms can then be diluted with the same or different formulation adjuvants to active ingredient concentrations that are suitable for practical use, and such concentrations are normally in the low range of the above concentration interval.
  • Emulsifiable concentrates generally contain 5 to 85 percent by weight, preferably 25 to 75 percent by weight, of the compound (s) according to the invention.
  • Ready-to-use solutions, emulsions and suspensions which are suitable, for example, as spray liquors, are suitable as use forms.
  • spray liquors for example, concentrations between 0.0001 and 20 percent by weight available.
  • spray liquors can be formulated in which the active compound concentration is preferably from 0.5 to 20 percent by weight, while the spray liquors formulated in the low-volume process and in the high-volume process preferably have an active compound concentration of 0. 02 to 1.0 or 0.002 to 0.1 percent by weight.
  • the fungicidal compositions according to the invention can be prepared by mixing at least one compound according to the invention with formulation auxiliaries.
  • the preparation of the agents can be carried out in a known manner, e.g. by mixing the active ingredient with solid carriers, by dissolving or suspending in suitable solvents or dispersing agents, possibly using surfactants as wetting agents or emulsifiers or dispersing agents, by diluting previously prepared emulsifiable concentrates with solvents or dispersing agents, etc.
  • the active ingredient can be mixed with a solid carrier, e.g. by grinding together; or you can impregnate the solid carrier with a solution or suspension of the active ingredient and then remove the solvent or dispersant by evaporation, heating or by suction under reduced pressure.
  • a solid carrier e.g. by grinding together; or you can impregnate the solid carrier with a solution or suspension of the active ingredient and then remove the solvent or dispersant by evaporation, heating or by suction under reduced pressure.
  • surfactants or dispersing agents such powdery agents can be made easily wettable with water, so that they can be dissolved in aqueous suspensions, e.g. suitable as a spray, can be transferred.
  • the compounds of the invention can also be mixed with a surfactant and a solid carrier to form a wettable powder which is dispersible in water, or they can be mixed with a solid pre-granulated carrier to form a granular product.
  • a compound according to the invention can be dissolved in a water-immiscible solvent, such as, for example, an alicyclic ketone, which advantageously contains dissolved emulsifier, so that the solution has a self-emulsifying effect when added to water.
  • a water-immiscible solvent such as, for example, an alicyclic ketone, which advantageously contains dissolved emulsifier, so that the solution has a self-emulsifying effect when added to water.
  • the active ingredient can be mixed with an emulsifier and the mixture can then be diluted with water to the desired concentration.
  • the active ingredient can be dissolved in a solvent and then mixed with an emulsifier.
  • Such a mixture can also be diluted with water to the desired concentration. In this way, emulsifiable concentrates or ready-to-use emulsions are contained.
  • the agents according to the invention can be used according to the application methods customary in crop protection or in agriculture.
  • the method according to the invention for combating fungi is characterized in that the goods to be protected, e.g. Plants, parts of plants or seeds, treated with an effective amount of a compound or agent according to the invention.
  • An emulsifiable concentrate has the following composition: g / liter Active ingredient (compound according to the invention) 100 Nonylphenol (10) ethoxylate (non-ionic emulsifier) 50 Calcium dodecylbenzenesulfonate (anionic emulsifier) 25 N-methyl-2-pyrrolidone (solubilizer) 200 Mixture of alkylbenzenes (solvents) ad 1 l
  • the active ingredient and the emulsifiers are dissolved in the solvent and in the solubilizer.
  • a ready-to-use spray mixture of any concentration can be prepared by emulsifying this concentrate in water.
  • a pointed powder has the following composition: Wt .-% Active ingredient (compound according to the invention) 25.0 Silica (hydrated: carrier) 20.0 Sodium lauryl sulfate (wetting agent) 2.0 Sodium lignosulfonate (dispersant) 4.0 Kaolin (carrier) 49.0
  • the components are mixed together and the whole is finely ground in a suitable mill. Dispersing the mixture in water results in a suspension that is suitable as a ready-to-use spray mixture.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
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  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Saccharide Compounds (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Escalators And Moving Walkways (AREA)

Description

  • Die vorliegende Erfindung betrifft substituierte 2-Phenyl-3-methoxyacrylsäuremethylester der allgemeinen Formel in welcher R1 und R2 die folgenden Bedeutungen haben:
    R 1 R 2
    3,5-Di(trifluormethyl)-phenyl Methyl
    2-Fluor-5-methylphenyl Methyl
    2-Benzofuranyl Methyl
    2-Chinolinyl Wasserstoff
    4-Fluorphenyl Methyl
    4-Nitrophenyl Methyl
    4-Chlorphenyl Methyl
    4-Chlorphenyl Aethyl
    β-Phenyläthenyl Methyl
    o-Tolyl Methyl
    p-Anisyl Methyl
    4-Biphenylyl Methyl
    Cyclopropyl Cyclopropyl
    β-(2-Furyl)-äthenyl Methyl
    β-(3,4,5-Trimethoxy-phenyl)-äthenyl Methyl
    α, α, α,-Trifluor-m-tolyl Methyl
    3-Bromphenyl Methyl
    2-Chlorphenyl Methyl
    3-Nitrophenyl Methyl
    5-Chlor-3-methyl-2-benzothienyl Methyl
    3-Chlorphenyl Methyl
    3,4-Dichlorphenyl Methyl
    2,4-Dichlorphenyl Methyl
    2,4-Dichlorphenyl 3-Pyridylmethyl
    3-Methyl-2-benzothienyl Methyl
    2,5-Dichlorphenyl Methyl
    4-Aethylphenyl Methyl
    3-Aethylphenyl Methyl
    3,4-Dimethylphenyl Methyl
    6-Methyl-2-naphthyl Methyl
    4-Difluormethoxyphenyl Methyl
    4-Chlorphenyl Neopentyl
    3,5-Di(trifluormethyl)-phenyl Aethyl
    3-Phenanthryl Methyl
    2-Fluorenyl Methyl
    Isopropyl Methyl
    4-Chlorphenyl n-Propyl
    4-Chlorphenyl Cyclopropyl
    3-Chlorphenyl Aethyl
    4-Fluorphenyl Aethyl
    4-Bromphenyl Aethyl
    4-tert.-Butylphenyl Methyl
    Cyclopropyl Methyl
    2-Chinolinylmethyl Methyl
    3-Fluor-5-trifluormethyl-phenyl Methyl
    3,5-Difluorphenyl Methyl
    3,5-Difluorphenyl Aethyl
    2-Fluorphenyl Aethyl
    3,4-Dimethoxyphenyl Methyl
    p-Tolyl Aethyl
    3-Trifluormethoxyphenyl Methyl
    3-Fluor-5-trifluormethyl-phenyl Aethyl
    Cyclohexyl Methyl
    4-Chlorphenyl Trifluormethyl
    3,4-Dimethoxybenzyl Methyl
    α, α, α,-Trifluor-m-tolyl Trifluormethyl
    α, α, α,-Trifluor-m-tolyl Aethyl
    3,5-Dichlorphenyl Methyl
    β-(2-Naphthyl)-äthenyl Trifluormethyl
    Methyl Methyl
    α, α, α,-Trifluor-m-tolyl n-Propyl
    α, α, α,-Trifluor-m-tolyl Cyclopropyl
    2-Chlor-5-trifluormethyl-phenyl Methyl
    2-Methylthio-5-trifluormethylphenyl Methyl
    4-Chlor-3-trifluormethyl-benzyl Methyl
    4-Methoxybenzyl Methyl
    α, α, α,-Trifluor-m-tolyl Isopropyl
    α, α, α,-Trifluor-m-tolyl α, α, α,-Trifluor-m-tolyl
    4-Äthoxyphenyl Methyl
    3-Chlor-4-fluorphenyl Methyl
    2,3-Dichlorphenyl Methyl
    p-Tolyl Trifluormethyl
    4-(2,4-Dichlorphenoxy)-phenyl Methyl
    4-(4-Nitrophenoxy)phenyl Methyl
    4-(4-Methoxyphenoxy)-phenyl Methyl
    3,4-Methylendioxyphenyl Methyl
    7-Benzodioxanyl Methyl
    3-Bromphenyl Aethyl
    3-Fluor-5-trifluormethylphenyl Cyclopropyl
    2,3,4-Trichlorphenyl Methyl
    4-Chlor-3-methylphenyl Methyl
    p-Tolyl n-Propyl
    4-Phenoxyphenyl Cyclopropyl
    3-Bromphenyl Cyclopropyl
    3-Chlorphenyl Cyclopropyl
    3-Fluorphenyl Cyclopropyl
    3-Bromphenyl n-Propyl
    3-Chlorphenyl n-Propyl
    4-Fluor-3-trifluormethylphenyl n-Propyl
    3-Fluorphenyl n-Propyl
    4-Phenoxyphenyl n-Propyl
    3-Fluor-5-trifluormethylphenyl n-Propyl
    3-Bromphenyl Trifluormethyl
    3-Chlorphenyl Trifluormethyl
    4-Phenoxyphenyl Trifluormethyl
    3-Bromphenyl Isopropyl
    3-Chlorphenyl Isopropyl
    4-Phenoxyphenyl Isopropyl
    4-Fluor-3-trifluormethylphenyl Cyclopropyl
    4-Fluorphenyl Cyclopropyl
    4-(n-Propyl)-phenyl Methyl
    4-Methoxy-3-nitrophenyl Methyl
    2,4-Dimethoxyphenyl Methyl
    4-Fluor-3-trifluormethylphenyl Isopropyl
    3-Iodphenyl Methyl
    4-Iodphenyl Methyl
    2-(4-Methoxyphenyl)äthyl Methyl
    1,4,8-Trimethyl-nona-1,3,7-trienyl Methyl
    1-Methyl-2-(3,4-methylendioxyphenyl)äthyl Methyl
  • Die erfindungsgemäßen Verbindungen besitzen fungizide Eigenschaften und eignen sich als fungizide Wirkstoffe, insbesondere zur Verwendung in der Landwirtschaft und im Gartenbau.
  • Die Erfindung betrifft ferner ein Verfahren zur Herstellung der erfindungsgemäßen Verbindungen, fungizide Mittel, die solche Verbindungen als Wirkstoffe enthalten, sowie die Verwendung solcher Verbindungen und Mittel zur Bekämpfung von Fungi in der Landwirtschaft und im Gartenbau.
  • Falls in den Verbindungen der Formel I' asymmetrische Kohlenstoffatome vorliegen, treten die Verbindungen in optisch aktiver Form auf. Allein aufgrund des Vorhandenseins der aliphatischen und der Imino-Doppelbindung treten die Verbindungen auf jeden Fall in der [E]- oder [Z]-Form auf. Ferner kann Atropisomerie auftreten. Die Formel I' soll all diese möglichen isomeren Formen sowie deren Gemische, z.B. racemische Gemische und beliebige [E/Z]-Gemische, umfassen.
  • In der unter Art. 54(3) EPUe zitierten EP-A 370 629, die der Schutzumfang vorliegender Erfindung abgegrenzt wurde, werden Fungizide/Insektizide auf Basis von Methoxyacrylat-Derivaten mit teilweise ähnlicher Struktur beschrieben.
  • Im Allgemeinen sind die [E]-Formen der Verbindungen der Formel I' gegenüber den [Z]-Formen bevorzugt.
  • Das erfindungsgemäße Verfahren zur Herstellung der erfindungsgemäßen Verbindungen ist dadurch gekennzeichnet, dass man ein Oxim X-OH der allgemeinen Formel worin
    • R1 und R2
    die oben angegebenen Bedeutungen besitzen,
    mit einem Benzylalkoholderivat der allgemeinen Formel worin
    U
    eine Abgangsgruppe bedeutet,
    umsetzt.
  • Bei dieser Umsetzung handelt es sich um eine nucleophile Substitution, die unter den diesbezüglich üblichen Reaktionsbedingungen durchgeführt werden kann. Unter der im Benzylalkoholderivat der Formel (III) vorhandenen Abgangsgruppe U ist vorzugsweise Chlor, Brom, Iod, Mesyloxy oder Tosyloxy zu verstehen. Die Umsetzung erfolgt zweckmäßigerweise in einem inerten organischen Verdünnungsmittel, wie einem cyclischen Ether, z.B. Tetrahydrofuran oder Dioxan, Aceton, Dimethylformamid oder Dimethylsulfoxid, in Gegenwart einer Base, wie Natriumhydrid, Natrium- oder Kaliumcarbonat, eines tertiären Amins, z.B. eines Trialkylamins, insbesondere Diazabicyclononan oder Diazabicycloundecan, oder Silberoxid, bei Temperaturen zwischen -20°C und 80°C, vorzugsweise im Temperaturbereich von 0°C bis 20°C.
  • Als Alternative kann die Umsetzung unter Phasentransferkatalyse in einem organischen Lösungsmittel, wie beispielsweise Methylenchlorid, in Gegenwart einer wässrigen basischen Lösung, z.B. Natriumhydroxidlösung, sowie eines Phasentransferkatalysators, wie beispielsweise Tetrabutylammoniumhydrogensulfat, bei Raumtemperatur erfolgen.
  • Die Isolierung und Reinigung der so hergestellten Verbindungen der Formel I' kann nach an sich bekannten Methoden erfolgen. Ebenfalls nach an sich bekannten Methoden können allfällig erhaltene Isomerengemische, z.B. E/Z-Isomerengemische, in die reinen Isomeren aufgetrennt werden, beispielsweise durch Chromatographie oder fraktionierte Kristallisation.
  • Die als Ausgangsmaterialien im erfindungsgemäßen Verfahren verwendeten Oxime X-OH, z.B. der Formel (II), sind entweder bekannt oder können nach an sich bekannten Methoden hergestellt werden, beispielsweise durch Umsetzung der entsprechenden Carbonylverbindung R1R2C=O mit Hydroxylaminhydrochlorid in Gegenwart einer Base, z.B. Natrium- oder Kaliumhydroxid oder Pyridin. Weitere Methoden finden sich in Houben-Weyl, "Methoden der Organischen Chemie", Band X/4, Seiten 3 - 308 (1968) ("Herstellung und Umwandlung von Oximen").
  • Ebenfalls können die Ausgangsmaterialien der Formel (III) auf an sich bekannte Weise hergestellt werden, z.B. wie in der europäischen Patentpublikation Nr. 203.606 (BASF) und in der dort zitierten Literatur beschrieben.
  • Die erfindungsgemäßen Verbindungen besitzen fungizide Wirkung und können dementsprechend zur Bekämpfung von Pilzen in der Landwirtschaft, im Gartenbau sowie in der Holzverarbeitung Verwendung finden. Sie eignen sich insbesondere zur Hemmung des Wachstums oder zu Vernichtung von phytopathogenen Pilzen auf Pflanzenteilen, z.B. Blättern, Stängeln, Wurzeln, Knollen, Früchten oder Blüten, und auf Saatgut sowie von im Erdboden auftretenden Schadpilzen. Ferner können mit den erfindungsgemäßen Verbindungen holzabbauende und holzverfärbende Pilze bekämpft werden. Die erfindungsgemäßen Verbindungen sind beispielsweise wirksam bei der Bekämpfung von Pilzen der Klassen Deuteromycetes, Ascomycetes, Basidiomycetes and Phycomycetes.
  • Besonders eignen sich die erfindungsgemäßen Verbindungen zur Bekämpfung der folgenden Schaderreger:
    • Echte Mehltaupilze (z.B. Erysiphe graminis, Erysiphe cichoracearum, Podosphaera leucotricha, Unicinula necator, Sphaerotheca spp.)
    • Rostpilze (z.B. Puccinia tritici, Puccinia recondita, Puccinia hordei, Puccinia coronata, Puccinia striiformos, Puccinia arachidis, Hermileia vastatrix, Urommyces fabae)
    • Schorfpilze (z.B. Venturia inaequalis)
    • Cercospora spp. (z.B. Cercospora arachidicola, Cercospora beticola)
    • Mycosphaerella spp. (z.B. Mycosphaerella fijiensis)
    • Atemaria spp. (z.B. Alternaria brassicae, Alternaria mali)
    • Septoria spp. (z.B. Septoria nodorum)
    • Heminthosporium spp. (z.B. Helminthosporium teres, Helminthosporium oryzae)
    • Plasmopara spp. (z.B. Plasmopara viticola)
    • Pseudoperonospora (z.B. Pseudoperonospora cubensis)
    • Phythophtora spp. (z.B. Phytophtora infestans)
    • Pseudocercosporella spp. (z.B. Pseudocercosporella herpotrichoides)
    • Piricularia spp. (z.B. Piricularia oryzae)
  • Ferner wirken die Verbindungen beispielsweise gegen Pilze der Gattungen Tilletia, Ustilago, Rhizotonia, Verticillium, Fusarium, Pythium, Gaeumannomyces, Sclerotinia, Monilia, Botrytis, Peronospora, Bremia, Gloeosporium, Cercosporidium, Penicillium, Ceratocystis, Rhynchosporium, Pyrenophora, Diaporthe, Ramularia und Leptosphaeria. Gewisse Vertreter der erfindungsgemäßen Verbindungen besitzen zudem Wirkung gegen holzschädigende Pilze, wie beispielsweise der Gattungen, Coniophora, Gloeophyllum, Poria, Merulius, Trametes, Aureobasidium, Sclerophoma und Trichoderma.
  • Die erfindungsgemäßen Verbindungen zeichnen sich durch prophylaktische und kurative Wirkung aus. Die erfindungsgemäßen Verbindungen wirken gegen phytopathogene Pilze unter Gewächshausbedingungen bereits bei Konzentrationen von 0,5 mg bis 500 mg Wirkstoff pro Liter Spritzbrühe. Im Freiland werden vorteilhaft Dosierungen von 20 g bis 1 kg Wirkstoff der Formel I' pro Hektar und Behandlung zur Anwendung gebracht. Zur Bekämpfung von samen- oder bodenbürtigen Pilzen im Beizverfahren werden mit Vorteil Dosierungen von 0,01 g bis 1,0 g Wirkstoff der Formel I' pro kg Samen verwendet.
  • Die erfindungsgemäßen Verbindungen können zu verschiedenen Mitteln, z.B. Lösungen, Suspensionen, Emulsionen, emulgierbaren Konzentraten und pulverförmigen Präparaten, formuliert werden. Die erfindungsgemäßen fungiziden Mittel sind dadurch gekennzeichnet, dass sie eine wirksame Menge mindestens einer Verbindung der allgemeinen Formel I', wie oben definiert, sowie Formulierungshilfsstoffe enthalten. Die Mittel enthalten zweckmäßigerweise zumindest einen der folgenden Formulierungshilfsstoffe:
    • Feste Trägerstoffe; Lösungs- bzw. Dispersionsmittel; Tenside (Netzmittel und Emulgatoren); Dispergiermittel (ohne Tensidwirkung); und Stabilisatoren.
  • Als feste Trägerstoffe kommen im wesentlichen in Frage: natürliche Mineralstoffe, wie Kaolin, Tonerden, Kieselgur, Talkum, Bentonit, Kreide, z.B. Schlämmkreide, Magnesiumcarbonat, Kalkstein, Quarz, Dolomit, Attapulgit, Montmorillonit und Diatomeenerde; synthetische Mineralstoffe, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate: organische Stoffe, wie Cellulose, Stärke, Harnstoff und Kunstharze; und Düngemittel, wie Phosphate und Nitrate, wobei solche Trägerstoffe z.B. als Granulate oder Pulver vorliegen können.
  • Als Lösungs- bzw. Dispersionsmittel kommen in wesentlichen in Frage: Aromaten, wie Toluol, Xylole, Benzol und Alkylnaphthaline; chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene und Methylenchlorid; aliphatische Kohlenwasserstoffe, wie Cyclohexan und Paraffine, z.B. Erdölfraktionen; Alkohole, wie Butanol und Glykol, sowie deren Ether und Ester; Ketone, wie Aceton, Methylethylketon, Methylisobutylketon und Cyclohexanon; und stark polare Lösungs- bzw. Dispersionsmittel, wie Dimethylformamid, N-Methylpyrrolidon und Dimetyhylsulfoxid, wobei solche Lösungs- bzw. Dispersionsmittel vorzugsweise Flammpunkte von mindestens 30°C und Siedepunkte von mindestens 50°C aufweisen, und Wasser. Unter den Lösungs- bzw. Dispersionsmitteln kommen auch in Frage sogenannte verflüssigte gasförmige Streckmittel oder Trägerstoffe, die solche Produkte sind, welche bei Raumtemperatur und unter Normaldruck gasförmig sind. Beispiele solcher Produkte sind insbesondere Aerosol-Treibgase, wie Halogenkohlenwasserstoffe, z.B. Dichlordifluormethan. Im Falle der Benutzung von Wasser als Lösungsmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden.
  • Die Tenside (Netzmittel und Emulgatoren) können nicht ionische Verbindungen sein, wie Kondensationsprodukte von Fettsäuren, Fettalkoholen oder fettsubstituierten Phenolen mit Ethylenoxid, Fettsäureester und -ether von Zuckern oder mehrwertigen Alkoholen; die Produkte, die aus Zuckern oder mehrwertigen Alkoholen durch Kondensation mit Ethylenoxid enthalten werden; Blockpolymere von Ethylenoxid und Propylenoxid; oder Alkyldimethylaminoxide.
  • Die Tenside können auch anionische Verbindungen darstellen, wie Seifen; Fettsulfatester, z.B. Dodecylnatriumsulfat, Octadecylnatriumsulfat und Cetylnatriumsulfat; Alkylsulfonate, Arylsulfonate und fettaromatische Sulfonate, wie Alkylbenzolsulfonate, z.B. Calcium-dodecylbenzolsulfonat; und Butylnaphthalinsulfonate; und komplexere Fettsulfonate, z.B. die Amidkondensationsprodukte von Ölsäure und N-Methyltaurin und das Natriumsulfonat von Dioctylsuccinat.
  • Die Tenside können schließlich kationische Verbindungen sein, wie Alkyldimethylbenzylammoniumchloride, Dialkyldimethylammoniumchloride, Alkyltrimethylammoniumchloride und ethoxylierte quaternäre Ammoniumchloride.
  • Als Dispergiermittel (ohne Tensidwirkung) kommen im wesentlichen in Frage: Lignin, Natrium- und Ammoniumsalze von Ligninsulfonsäure, Natriumsalze von Maleinsäureanhydrid-Diisobutylen-Copolymeren, Natrium- und Ammoniumsalze von sulfonierten Polykondensationsprodukten aus Naphthalin und Formaldehyd und Sulfitablaugen.
  • Als Dispergiermittel, die sich insbesondere als Verdickungs- bzw. Antiabsetzmittel eignen, können z.B. Methylcellulose, Carboxymethylcellulose, Hydroxyethylcellulose, Polyvinylalkohol, Alginate, Caseinate und Blutalbumin eingesetzt werden.
  • Beispiele von geeigneten Stabilisatoren sind säurebindende Mittel, z.B. Epichlorhydrin, Phenylglycidether und Soyaepoxide, Antioxadantien, z.B. Gallusäureester und Butylhydroxytoluol; UV-Absorber, z.B. substituierte Benzophenone, Diphenylacrylnitrilsäureester und Zimtsäureester; und Deskativatoren, z.B. Salze der Ethylendiamintetraessigsäure und Polyglykole.
  • Die erfindungsgemäßen fungiziden Mittel können neben den Wirkstoffen der Formel I' auch andere Wirkstoffe enthalten, z.B. anderweitige fungizide Mittel, insektizide und akarizide Mittel, Bakterizide, Pflanzenwachstumsregulatoren und Düngemittel. Solche Kombinationsmittel eignen sich zur Verbreitung des Wirkungsspektrum oder zur spezifischen Beeinflussung des Pflanzenwachstums.
  • Im Allgemeinen enthalten die erfindungsgemäßen fungiziden Mittel, je nach deren Art, zwischen 0,0001 und 85 Gewichtsprozent an erfindungsgemäßer Verbindungen als Wirkstoff(en). Sie können in einer Form vorliegen, die sich für die Lagerung und den Transport eignet. In solchen Formen, z.B. emulgierbaren Konzentraten, ist die Wirkstoffkonzentration normalerweise im höheren Bereich des obigen Konzentrationsintervalls. Diese Formen können dann mit gleichen oder verschiedenen Formulierungshilfsstoffen bis zu Wirkstoffkonzentrationen verdünnt werden, die sich für den praktischen Gebrauch eignen, und solche Konzentrationen liegen normalerweise im niedrigen Bereich des obigen Konzentrationsintervalls. Emulgierbare Konzentrate enthalten im Allgemeinen 5 bis 85 Gewichtsprozent vorzugsweise 25 bis 75 Gewichtsprozent, der erfindungsgemäßen Verbindung(en). Als Anwendungsformen kommen u.a. gebrauchsfertige Lösungen, Emulsionen und Suspensionen, die sich beispielsweise als Spritzbrühen eignen, in Frage. In solchen Spritzbrühen können z.B. Konzentrationen zwischen 0,0001 und 20 Gewichtsprozent vorliegen. Im Ultra-Low-Volume-Verfahren können Spritzbrühen formuliert werden, in denen die Wirkstoffkonzentration vorzugsweise von 0,5 bis 20 Gewichtsprozent beträgt, während die im Low-Volume-Verfahren und im High-Volume-Verfahren formulierten Spritzbrühen vorzugsweise eine Wirkstoffkonzentration von 0,02 bis 1,0 bzw. 0,002 bis 0,1 Gewichtsprozent aufweisen.
  • Die erfindungsgemäßen fungiziden Mittel können dadurch hergestellt werden, dass man mindestens eine erfindungsgemäße Verbindung mit Formulierungshilfsstoffen vermischt.
  • Die Herstellung der Mittel kann in bekannter Weise durchgeführt werden, z.B. durch Vermischen des Wirkstoffes mit festen Trägerstoffen, durch Auflösen oder Suspendieren in geeigneten Lösungs- bzw. Dispersionsmittel, eventuell unter Verwendung von Tensiden als Netzmittel oder Emulgatoren oder von Dispergiermitteln, durch Verdünnen bereits vorbereiteter emulgierbarer Konzentrate mit Lösungs- bzw. Dispergiermitteln usw.
  • Im Falle von pulverförmigen Mitteln kann der Wirkstoff mit einem festen Trägerstoff vermischt werden, z.B. durch Zusammenmahlen; oder man kann den festen Trägerstoff mit einer Lösung oder Suspension des Wirkstoffs imprägnieren und dann das Lösungs- bzw. Dispersionsmittel durch Abdunsten, Erhitzen oder durch Absaugen unter vermindertem Druck entfernen. Durch Zusatz von Tensiden bzw. Dispergiermitteln kann man solche pulverförmige Mittel mit Wasser leicht benetzbar machen, so dass sie in wässrige Suspensionen, die sich z.B. als Spritzmittel eignen, überführt werden können.
  • Die erfindungsgemäßen Verbindungen können auch mit einem Tensid und einem festen Trägerstoff zur Bildung eines netzbaren Pulvers vermischt werden, welches in Wasser dispergierbar ist, oder sie können mit einem festen vorgranulierten Trägerstoff zur Bildung eines granulatförmigen Produktes vermischt werden.
  • Wenn gewünscht, kann eine erfindungsgemäße Verbindung in einem mit Wasser nicht mischbaren Lösungsmitteln, wie beispielsweise einem alicyclischen Keton, gelöst werden, das zweckmäßigerweise gelösten Emulgator enthält, so dass die Lösung bei Zugabe zu Wasser selbstemulgierend wirkt. Andernfalls kann der Wirkstoff mit einem Emulgator vermischt und das Gemisch dann mit Wasser auf die gewünschte Konzentration verdünnt werden. Zudem kann der Wirkstoff in einem Lösungsmittel gelöst und danach mit einem Emulgator gemischt werden. Ein solches Gemisch kann ebenfalls mit Wasser auf die gewünschte Konzentration verdünnt werden. Auf diese Weise enthält man emulgierbare Konzentrate bzw. gebrauchsfertige Emulsionen.
  • Die Verwendung der erfindungsgemäßen Mittel kann nach den im Pflanzenschutz bzw. in der Landwirtschaft üblichen Applikationsmethoden erfolgen. Das erfindungsgemäße Verfahren zur Bekämpfung von Fungi ist dadurch gekennzeichnet, dass man das zu schützende Gut, z.B. Pflanzen, Pflanzenteile bzw. Samen, mit einer wirksamen Menge einer erfindungsgemäßen Verbindung bzw. eines erfindungsgemäßen Mittels behandelt.
  • Die nachstehenden Beispiele illustrieren die Erfindung.
    • I. Herstellung der Wirkstoffe der Formel I' Beispiel 1 (Herstellungsbeispiel außerhalb des stofflichen Umfangs der Erfindung)
  • Zu 0,19 g (7,7 mMol) Natriumhydrid in 20 ml Dimethylformamid gibt man bei 0°C 2,0 g (7,0 mMol) 2-(α-Brom-o-tolyl)-3-methoxyacrylsäure-methylester und 0,95 g (7,0 mMol) Acetophenonoxim. Nach 10-minütigem Rühren des Reaktionsgemisches wird gesättigte Natriumhydrogencarbonatlösung zugegeben und das Gemisch dreimal mit Ethylacetat extrahiert. Die organischen Phasen werden über wasserfreiem Natriumsulfat getrocknet. Nach Abdestillieren des Lösungsmittels wird das zurückbleibende Öl an Kieselgel unter Verwendung von Diethylether/n-Hexan (1:1) als Laufmittel chromtographisch gereinigt. Man erhält auf diese Weise den [E]-3-Methoxy-2-[α-{[(methylbenzyl)imino]oxy}-o-tolyl)-acrylsäure-methylester als gelbes Öl.
    • Beispiel 2 (Herstellungsbeispiel außerhalb des stofflichen Umfangs der Erfindung)
  • 3,67 g (13,2 mMol) 2-(α-Brom-o-tolyl)-3-methoxyacrylsäure-methylester und 3,0 g (13,2 mMol) 4-Phenoxyacetophenonoxim in 13 ml Methylenchlorid werden mit 13 ml 2,2 N Natriumhydroxidlösung und 5,7 g gleichen Tetrabutylammoniumhydrogensulfat in 10 Minuten bei Raumtemperatur intensiv gerührt. Dann gibt man die gleichen Mengen Methylenchlorid, 2,2 N Natriumhydroxidlösung und Tetrabutylammoniumhydrogensulfat hinzu und rührt weitere 10 Minuten. Anschließend werden nochmals die gleichen Mengen 2,2 N Natriumhydroxidlösung und Tetrabutylammoniumhydrogensulfat zugegeben und nach weiteren 10 Minuten Rühren gesättigte Natriumhydrogencarbonatlösung.
  • Man extrahiert das Gemisch dreimal mit Aethylacetat, wäscht die vereinigten organischen Phasen mit gesättigter Natriumchloridlösung und trocknet sie über wasserfreiem Natriumsulfat. Nach Abdestillieren des Lösungsmittels wird das zurückbleibende Öl an Kieselgel unter Verwendung von n-Hexan/Diethylether (1:1) als Laufmittel chromatographisch gereinigt:
  • Auf diese Weise erhält man den [E]-3-Methoxy-2-{α-{[(α-methyl-4-phenoxybenzyl)imino]oxy}-o-tolyl]-acrylsäure-methylester als gelbes Öl.
    • Beispiel 3 - 123
  • Analog dem Beispiel 1 ("Methode 1") oder Beispiel 1 ("Methode 2") beschriebenen Verfahren erhält man ausgehend von 2-(α-Brom-o-tolyl)-3-methoxyacrylsäuremethylester und dem entsprechenden Oxim der Formel II die in der nachfolgenden Tabelle aufgeführten Verbindungen der Formel I':
    • II. Formulierungsbeispiele: Beispiel 245
  • Ein emulgierbares Konzentrat hat folgende Zusammensetzung:
    g/Liter
    Wirkstoff (erfindungsgemäße Verbindung) 100
    Nonylphenol-(10)äthoxylat (nicht ionischer Emulgator) 50
    Calcium-dodecylbenzolsulfonat (anionischer Emulgator) 25
    N-Methyl-2-pyrrolidon (Lösungsvermittler) 200
    Gemisch von Alkylbenzolen (Lösungsmittel) ad 1 l
  • Der Wirkstoff und die Emulgatoren werden im Lösungsmittel und im Lösungsvermittler gelöst. Durch Emulgieren dieses Konzentrates in Wasser kann eine gebrauchsfertige Spritzbrühe beliebiger Konzentration hergestellt werden.
    • Beispiel 246
  • Ein Spitzpulver hat folgende Zusammensetzung:
    Gew.-%
    Wirkstoff (erfindungsgemäße Verbindung) 25,0
    Kieselsäure (hydratisiert: Trägerstoff) 20,0
    Natrium-laurylsulfat (Netzmittel) 2,0
    Natrium-lignosulfonat (Dispergiermittel) 4,0
    Kaolin (Trägerstoff) 49,0
  • Die Komponenten werden miteinander vermischt, und das ganze wird in einer geeigneten Mühle feingemahlen. Durch Dispergieren des Gemisches in Wasser ergibt sich eine Suspension, die sich als gebrauchsfertige Spritzbrühe eignet.

Claims (5)

  1. Verbindungen der allgemeinen Formel in welcher R1 und R2 die folgenden Bedeutungen haben: R 1 R 2 3,5-Di(trifluormethyl)-phenyl Methyl 2-Fluor-5-methylphenyl Methyl 2-Benzofuranyl Methyl 2-Chinolinyl Wasserstoff 4-Fluorphenyl Methyl 4-Nitrophenyl Methyl 4-Chlorphenyl Methyl 4-Chlorphenyl Aethyl β-Phenyläthenyl Methyl o-Tolyl Methyl p-Anisyl Methyl 4-Biphenylyl Methyl Cyclopropyl Cyclopropyl β-(2-Furyl)-äthenyl Methyl β-(3,4,5-Trimethoxy-phenyl)-äthenyl Methyl α, α, α,-Trifluor-m-tolyl Methyl 3-Bromphenyl Methyl 2-Chlorphenyl Methyl 3-Nitrophenyl Methyl 5-Chlor-3-methyl-2-benzothienyl Methyl 3-Chlorphenyl Methyl 3,4-Dichlorphenyl Methyl 2,4-Dichlorphenyl Methyl 2,4-Dichlorphenyl 3-Pyridylmethyl 3-Methyl-2-benzothienyl Methyl 2,5-Dichlorphenyl Methyl 4-Aethylphenyl Methyl 3-Aethylphenyl Methyl 3,4-Dimethylphenyl Methyl 6-Methyl-2-naphthyl Methyl 4-Difluormethoxyphenyl Methyl 4-Chlorphenyl Neopentyl 3,5-Di(trifluormethyl)-phenyl Aethyl 3-Phenanthryl Methyl 2-Fluorenyl Methyl Isopropyl Methyl 4-Chlorphenyl n-Propyl 4-Chlorphenyl Cyclopropyl 3-Chlorphenyl Aethyl 4-Fluorphenyl Aethyl 4-Bromphenyl Aethyl 4-tert.-Butylphenyl Methyl Cyclopropyl Methyl 2-Chinolinylmethyl Methyl 3-Fluor-5-trifluormethyl-phenyl Methyl 3,5-Difluorphenyl Methyl 3,5-Difluorphenyl Aethyl 2-Fluorphenyl Aethyl 3,4-Dimethoxyphenyl Methyl p-Tolyl Aethyl 3-Trifluormethoxyphenyl Methyl 3-Fluor-5-trifluormethyl-phenyl Aethyl Cyclohexyl Methyl 4-Chlorphenyl Trifluormethyl 3,4-Dimethoxybenzyl Methyl α, α, α,-Trifluor-m-tolyl Trifluormethyl α, α, α,-Trifluor-m-tolyl Aethyl 3,5-Dichlorphenyl Methyl β-(2-Naphthyl)-äthenyl Trifluormethyl Methyl Methyl α, α, α,-Trifluor-m-tolyl n-Propyl α, α, α,-Trifluor-m-tolyl Cyclopropyl 2-Chlor-5-trifluormethyl-phenyl Methyl 2-Methylthio-5-trifluormethylphenyl Methyl 4-Chlor-3-trifluormethyl-benzyl Methyl 4-Methoxybenzyl Methyl α, α, α,-Trifluor-m-tolyl Isopropyl α, α, α,-Trifluor-m-tolyl α, α, α,-Trifluor-m-tolyl 4-Äthoxyphenyl Methyl 3-Chlor-4-fluorphenyl Methyl 2,3-Dichlorphenyl Methyl p-Tolyl Trifluormethyl 4-(2,4-Dichlorphenoxy)-phenyl Methyl 4-(4-Nitrophenoxy)phenyl Methyl 4-(4-Methoxyphenoxy)-phenyl Methyl 3,4-Methylendioxyphenyl Methyl 7-Benzodioxanyl Methyl 3-Bromphenyl Aethyl 3-Fluor-5-trifluormethylphenyl Cyclopropyl 2,3,4-Trichlorphenyl Methyl 4-Chlor-3-methylphenyl Methyl p-Tolyl n-Propyl 4-Phenoxyphenyl Cyclopropyl 3-Bromphenyl Cyclopropyl 3-Chlorphenyl Cyclopropyl 3-Fluorphenyl Cyclopropyl 3-Bromphenyl n-Propyl 3-Chlorphenyl n-Propyl 4-Fluor-3-trifluormethylphenyl n-Propyl 3-Fluorphenyl n-Propyl 4-Phenoxyphenyl n-Propyl 3-Fluor-5-trifluormethylphenyl n-Propyl 3-Bromphenyl Trifluormethyl 3-Chlorphenyl Trifluormethyl 4-Phenoxyphenyl Trifluormethyl 3-Bromphenyl Isopropyl 3-Chlorphenyl Isopropyl 4-Phenoxyphenyl Isopropyl 4-Fluor-3-trifluormethylphenyl Cyclopropyl 4-Fluorphenyl Cyclopropyl 4-(n-Propyl)-phenyl Methyl 4-Methoxy-3-nitrophenyl Methyl 2,4-Dimethoxyphenyl Methyl 4-Fluor-3-trifluormethylphenyl Isopropyl 3-Iodphenyl Methyl 4-Iodphenyl Methyl 2-(4-Methoxyphenyl)äthyl Methyl 1,4,8-Trimethyl-nona-1,3,7-trienyl Methyl 1-Methyl-2-(3,4-methylendioxyphenyl)-äthyl Methyl
  2. Fungizides Mittel, dadurch gekennzeichnet, dass es eine wirksame Menge mindestens einer Verbindung gemäß Anspruch 1 sowie Formulierungshilfsstoffe enthält.
  3. Verfahren zur Herstellung einer Verbindung nach Anspruch 1 der allgemeinen Formel I' worin
    R1 und R2   die in Anspruch 1 angegebenen Bedeutungen haben,
    dadurch gekennzeichnet, dass man eine Verbindung der allgemeinen Formel worin
    R1 und R2   die in Anspruch 1 angegebenen Bedeutungen haben,
    mit einem Benzylalkoholderivat der allgemeinen Formel worin
    U   eine Abgangsgruppe bedeutet,
    umsetzt.
  4. Verfahren zur Bekämpfung von Fungi in der Landwirtschaft und im Gartenbau, dadurch gekennzeichnet, dass man das zu schützende Gut mit einer wirksamen Menge einer Verbindung gemäß Anspruch 1 bzw. eines Mittels gemäß Anspruch 1 behandelt.
  5. Verwendung einer Verbindung gemäß Anspruch 1 bzw. eines Mittels gemäß Anspruch 2 zur Bekämpfung von Fungi in der Landwirtschaft und im Gartenbau.
EP89913190A 1988-12-29 1989-12-12 Aldimino- oder ketimino-oxy-ortho-tolylacrylsäure-methylester, ihre herstellung und diese enthaltende fungizide Expired - Lifetime EP0403618B2 (de)

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PCT/CH1989/000216 WO1990007493A1 (de) 1988-12-29 1989-12-12 Aldimino- oder ketimino-oxy-ortho-tolylacrylsäure-methylester, ihre herstellung und diese enthaltende fungizide

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EP89913190A Expired - Lifetime EP0403618B2 (de) 1988-12-29 1989-12-12 Aldimino- oder ketimino-oxy-ortho-tolylacrylsäure-methylester, ihre herstellung und diese enthaltende fungizide

Country Status (17)

Country Link
EP (1) EP0403618B2 (de)
JP (1) JP2907540B2 (de)
KR (1) KR100187541B1 (de)
AT (1) ATE117983T1 (de)
AU (1) AU4639089A (de)
BR (1) BR8907287A (de)
CA (1) CA2005345A1 (de)
DE (1) DE58908972D1 (de)
DK (1) DK206290D0 (de)
ES (1) ES2067570T3 (de)
FI (1) FI904230A0 (de)
HU (1) HU216144B (de)
MX (1) MX9202638A (de)
NO (1) NO173543C (de)
NZ (1) NZ231891A (de)
PT (1) PT92753B (de)
WO (1) WO1990007493A1 (de)

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CZ419897A3 (cs) * 1995-06-27 1998-03-18 Novartis Ag Oximethery, způsob jejich přípravy a meziprodukty v tomto způsobu, pesticidní prostředky, které je obsahují a jejich použití
EA000435B1 (ru) * 1995-07-04 1999-08-26 Новартис Аг Бис-оксимовые производные триазолина и изоксазолина
GB9516788D0 (en) * 1995-08-16 1995-10-18 Agrevo Uk Ltd Fungicides
DE19539324A1 (de) * 1995-10-23 1997-04-24 Basf Ag Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel
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DK0876333T3 (da) * 1995-12-07 2002-07-22 Bayer Ag Fremgangsmåde til fremstilling af pesticider
PT865424E (pt) 1995-12-07 2003-02-28 Bayer Ag Pesticidas
WO1997029093A1 (de) 1996-02-05 1997-08-14 Basf Aktiengesellschaft Pyrimidinderivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel zur bekämpfung von tierischen schädlingen oder von schadpilzen
WO1997040671A1 (en) * 1996-04-26 1997-11-06 Novartis Ag Pesticidal compositions
US6084120A (en) * 1997-07-09 2000-07-04 Hoffmann-La Roche Inc. β-Alkoxyacrylates against malaria
CN1062711C (zh) 1998-02-10 2001-03-07 化工部沈阳化工研究院 不饱和肟醚类杀虫、杀真菌剂
EP0936213B1 (de) * 1998-02-10 2003-03-26 Dow AgroSciences LLC Ungesättigte Oxim-Ether und ihre Verwendung als Fungizide oder Insectizide
FR2777002A1 (fr) * 1998-04-07 1999-10-08 Rhone Poulenc Agrochimie Nouveaux composes fongicides
FR2777003A1 (fr) * 1998-04-07 1999-10-01 Rhone Poulenc Agrochimie Nouveaux composes fongicides
US6313344B1 (en) 1998-05-27 2001-11-06 Bayer Aktiengesellschaft Organic compounds
AU1007400A (en) * 1999-01-27 2000-08-03 Dow Agrosciences Llc Aryl and heteroarylcyclopropyl oxime ethers and their use as fungicides and insecticides
ES2211634T3 (es) * 1999-11-05 2004-07-16 Nippon Soda Co., Ltd. Compuestos oxima o-eter y fungicidas para su utilizacion en agricultura y horticultura.
EP1125931A1 (de) * 2000-02-17 2001-08-22 Hunan Research Institute of Chemical Industry Biozide Alkyl-substituierte (Hetero)aryl-ketoxim-O-ether und Verfahren zu ihrer Herstellung
CN1179942C (zh) * 2002-09-13 2004-12-15 湖南化工研究院 具有杀菌活性的含硫不饱和肟醚类化合物及其制备方法
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CN103601716A (zh) * 2013-11-20 2014-02-26 厦门大学 一种苯并噻吩取代肟醚类化合物及其制备方法与应用
CN103980179A (zh) * 2014-05-29 2014-08-13 厦门大学 一种吲哚取代肟醚类化合物及其制备方法与应用
MX2017015558A (es) * 2015-06-02 2018-02-23 Syngenta Participations Ag Composiciones para el control de vectores mosquitos, metodos y productos que utilizan las mismas.
WO2017129121A1 (zh) * 2016-01-26 2017-08-03 南开大学 一类噻二唑肟醚甲氧基丙烯酸酯衍生物及其制备方法和用途
WO2017129122A1 (zh) * 2016-01-26 2017-08-03 南开大学 一类异噻唑肟醚甲氧基丙烯酸酯衍生物及其制备方法和用途
CN106995417B (zh) 2016-01-26 2019-05-31 南开大学 一类异噻唑肟醚甲氧基丙烯酸酯衍生物及其制备方法和用途
RU2698300C1 (ru) * 2018-07-04 2019-08-26 Федеральное государственное бюджетное образовательное учреждение высшего образования "Российский химико-технологический университет имени Д.И. Менделеева" (РХТУ им. Д.И. Менделеева) Замещенные метил-n-метоксикарбаматы
AR115870A1 (es) 2018-07-31 2021-03-10 Sumitomo Chemical Co MÉTODO PARA CONTROLAR EL HONGO DE LA ROYA DE LA SOJA QUE TIENE RESISTENCIA AL INHIBIDOR DE SITIO Qₒ
JP2023022345A (ja) * 2020-01-31 2023-02-15 住友化学株式会社 植物病害防除組成物及び植物病害防除方法
EP3960727A1 (de) 2020-08-28 2022-03-02 Basf Se Verwendung von verbindungen vom strobilurintyp zur bekämpfung von phytopathogenen pilzen, die eine aminosäuresubstitution f129l im mitochondrialen cytochrom-b-protein enthalten, das resistenz gegenüber qo-inhibitoren vi verleiht
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Also Published As

Publication number Publication date
HU900284D0 (en) 1991-05-28
JP2907540B2 (ja) 1999-06-21
EP0403618B1 (de) 1995-02-01
EP0403618A1 (de) 1990-12-27
NZ231891A (en) 1992-08-26
CA2005345A1 (en) 1990-06-29
BR8907287A (pt) 1991-03-12
NO173543B (no) 1993-09-20
FI904230A7 (fi) 1990-08-27
MX9202638A (es) 1992-06-30
KR100187541B1 (ko) 1999-06-01
AU4639089A (en) 1990-08-01
HU216144B (hu) 1999-04-28
JPH03503056A (ja) 1991-07-11
ATE117983T1 (de) 1995-02-15
DK206290A (da) 1990-08-28
HUT55951A (en) 1991-07-29
DK206290D0 (da) 1990-08-28
NO903771D0 (no) 1990-08-28
WO1990007493A1 (de) 1990-07-12
PT92753A (pt) 1990-06-29
ES2067570T3 (es) 1995-04-01
NO173543C (no) 1993-12-29
FI904230A0 (fi) 1990-08-27
NO903771L (no) 1990-08-28
DE58908972D1 (de) 1995-03-16
KR910700228A (ko) 1991-03-14
PT92753B (pt) 1995-12-29

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